The objective of this work is to investigate the synthesis of structurally novel, fused heterocyclic systems for evaluation of their biological activity, particularly with respect to antibacterial and/or antifungal activity. This project should lead to a range of such structures based upon the results of the preliminary studies. The specific aims are to synthesize novel indole and indole-like, fused, medium-size ring heterocycles with the initial targets being indolobenzodiazocines and triazonines and indolopyridobenzazepines and diazocines. This will be accomplished via photolysis of pertinent chloroacetamides and the thermolysis or photolysis of their corresponding azidoacetamide analog precursors to fuse the "a" side and "a and i" sides of appropriately substituted indoles or indole-like molecules, or the "a" side of similarly substituted tetrahydro-beta-carbolines (THBCs) with 7-, 8-, or 9-membered benzazacyclic rings. The starting materials may be substituted with various groups (e.g. methoxy, hydroxy, halogen) in several positions (e.g. 5 and/or 6) that are known to be of importance in pharmacologically active and medicinal compounds. In order to accomplish these goals precursor 1-benzylic indole-like componds and THBCs will be prepared, converted to the chloroacetamides, and either photolyzed directly or converted to the respective azidoacetamides for subsequent thermolysis. The resulting lactams, themselves potentially active, will be reduced to the respective heterocyclic bases for final evaluation. In addition, other heterocyclic systems may be formed by cyclization reactions at adjacent sites that in themselves could be biologically significant. From all of these compounds can spring even more elaborate ring systems by the same sequence of reactions. There is the real possibility of preparing a variety of hitherto unreported nitrogen heterocycles whose biomedical relevance although unknown, have definite potential for drug-lead compound development. The product heterocycles will be submitted to the University of Wollongong, Australia, for testing for antibacterial and/or antifungal activity. In addition, they will be sent to the NCI anti-cancer and anti-HIV screens.